ANSWERED AirVPN app & Mac OS 10.11.3

[nunz 5]

I am behind a corporate firewall with the following setup in my office:

- Mac OS 10.11.3

- Air VPN.app 2.10.3

 

With all default settings, I cannot initiate a VPN session at all. It tries to connect to a recommended server, and just keeps trying without successfully establishing a connection.

 

When troubleshooting issues such as this, what would be a standard set of steps to take? Please advise.

[Khariz 109]

Go into the options of the client and try the SSL 443 setting.

[nunz 5]

Go into the options of the client and try the SSL 443 setting.

WOW. Khariz, I owe you a big thanks. As little as I know about these things, how did you know that SSL 443 would let me get out of my corporate wall? 

[Khariz 109]

Good question.  Simple answer.  In a basic sense, what happens when you select that option is this:  

 

A secure, encrypted tunnel is created between your computer and the VPN service PRIOR to the VPN service starting up.  Since the encrypted VPN tunnel that is subsequently created is itself inside of another encrypted tunnel, there's no way for the corporate network to inspect what type of connection it is to disallow it.  They just think you are talking over HTTPS to some website, or whatever.  They can't see the subsequent connection to the VPN.

[nunz 5]

Khariz - Thank you for taking the time to explain it to me in the kind of language I understand. 

 

Please allow me to review a few things in my office environment:

(1) Until this year, to the best of my knowledge, I was always able to initiate VPN connection with all settings in the clients in automatic.

(2) Starting this year, after a series of network "upgrades" were performed, my VPN connection could not get started.

(3) Now with your SSL 443 advice, I am successful in establishing VPN connection.

 

Would (1), (2), and (3) enough to assert that my work has specifically decided to disallow VPN connection?

Or, could this be a collateral inconvenience caused by something else that the IT has started doing.

Finally, what would normally be a primary reason for a corporate IT to disallow VPN from inside the firewall?

 

I hope I am not taking too much of your time, Khariz. But, I truly appreciate your educating me.

[CultureVulture 30]

And me! The thing about forums is, it's not just the initial poster that gets an education.

I got slightly lost, though. Are you saying the SSL 443 connection opens up the connection to the AirVPN before the corporate VPN establishes itself?

[Khariz 109]

Unfortunately, I really don't have enough information to answer the questions. I'd just be guessing. It's not highly unusual for companies to close gaps in their networks or to disallow VPN services, though. As to why? Well, it's the same reason that I disallow them on my network except for on my devices. I can't track what my daughter does on the Internet, if she's encrypting her content and making it appear that she is just connecting to a single IP for the duration of her Internet use. It would also allow her to circumvent any parental locks I have in place with regard to content.

 

Companies are the same. They may want to track what their employees do on the Internet, prevent the employees from visiting certain content, or prevent you from accessing certain content to prevent leaks of internal information, etc. I really don't know what your particular company's motives may be.

[Khariz 109]

And me! The thing about forums is, it's not just the initial poster that gets an education.

I got slightly lost, though. Are you saying the SSL 443 connection opens up the connection to the AirVPN before the corporate VPN establishes itself?

We aren't talking a corporate VPN. We are taking about the AirVPN VPN.